bis-(5'-deoxy-2',3'-O-isopropylidene-uridine)-5',5'-disulfide | 6991-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: bis-(5'-deoxy-2',3'-O-isopropylidene-uridine)-5',5'-disulfide
• 英文别名: O^{2'_,O3'_;O2'''_,O3'''}-diisopropylidene-5',5'''-disulfanediyl-bis-(5'-deoxy-uridine)；1-[(3aR,4R,6S,6aS)-6-[[[(3aR,4R,6S,6aS)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyldisulfanyl]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione
• CAS: 6991-86-2
• 化学式: C₂₄H₃₀N₄O₁₀S₂
• 分子量: 598.655
• InChiKey: VRERXLXAHRVSMV-LSRAZJPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  205
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  7-(4-甲基苯基)磺酰基-7-氮杂双环[4.1.0]庚烷 、 bis-(5'-deoxy-2',3'-O-isopropylidene-uridine)-5',5'-disulfide 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 乙腈 为溶剂， 反应 9.0h， 以72%的产率得到5'-(p-tolylsulfonamido-cyclohexylthio)-5'-deoxy-2',3'-O-isopropylidene-uridine
  参考文献：
  名称：

  Novel chalcogenides of thymidine and uridine: synthesis, properties and applications

  摘要：

  A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.02.035
• 作为产物：
  描述：

  2',3'-O-isopropylidene-5'-O-tosyluridine 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以77%的产率得到bis-(5'-deoxy-2',3'-O-isopropylidene-uridine)-5',5'-disulfide
  参考文献：
  名称：

  Novel chalcogenides of thymidine and uridine: synthesis, properties and applications

  摘要：

  A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.02.035

文献信息

• Novel chalcogenides of thymidine and uridine: synthesis, properties and applications
  作者：Kirubakaran Sivapriya、Perumal Suguna、S. Shubashree、Perali Ramu Sridhar、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2007.02.035

  日期：2007.7

  A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides. (C) 2007 Elsevier Ltd. All rights reserved.